期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 10, 期 21, 页码 4201-4207出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob25297j
关键词
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资金
- NSFC/China
- Shanghai Institutions of Higher Learning
- Program for New Century Excellent Talents in University (NCET)
- Innovation Program of Shanghai Municipal Education Commission
- Fundamental Research Funds for the Central Universities [WK1013002]
- SRFDP [200802510011, 20100074110015]
Cyanide sensing has attracted increasing interest due to its toxicity and wide use in industrial activities. Herein, we developed three colorimetric cyanide sensors by the modification of the alpha-position of a dipyrrin chromophore with various carbonyl groups, namely, C6F5CO, C6H5CO and CHO for 1, 2 and 3, respectively. In dichloromethane, these sensors respond to both CN- and F- with distinct colour changes. UV-Vis, H-1 NMR and HRMS measurements imply a two-process interaction between the sensors and CN-. Initially, CN- forms a hydrogen bond with the NH moiety, and then it attacks the carbonyl group of the sensors via a nucleophilic addition reaction. In contrast, in aqueous systems, only cyanide induced vivid solution colour changes from light yellow to pink via nucleophilic addition reactions. The CN- detection limits reach a micromolar level of 3.6 x 10(-6) M, 4.2 x 10(-6) M and 7.1 x 10(-6) M for 1, 2 and 3, respectively. In view of the easy synthesis and the highly selective recognition of CN- with vivid colour changes, 1-3 may be developed as a novel and promising prototype of selective and sensitive colorimetric cyanide sensors.
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